The two stories by O’Henry demonstrate the author’s skill in using irony. In the story, “The Last Leaf,” the young girl lays dying. She has given up any hope of recovery and watches the leaves as they fall from the vine. The painter who strives to save the girl by painting the last leaf that was about to fall off of the vine on the wall becomes ill in the process and dies. The young girl, having seen the leaf hanging on, begins to gain strength and lives.

In the story, "The Cop and the Anthem," Soapy, a derelict who sleeps on the park bench, has become tired of wrangling with newspapers to keep warm. He dreams of the island where he makes his annual pilgrimage in winter. However, the reader learns that the island is jail. Soapy knows what it takes to get himself arrested. He engages in various acts but is unable to accomplish his arrest. He hears music coming from a church and stops to listen to it. The music overwhelms him, and he makes the decision that the next day he will take action to change his life for the better and get a job. A police officer sees him loitering and arrests him. The irony is that he could not get himself arrested when he had tried, but once he makes a decision to turn his life around, he gets arrested.

Another commonality in the stories is that both characters have given up their quest, one toward life as she prepares for death, and the other no longer attempts to get himself arrested. In addition, O’Henry has used characters who are down in their luck economically, which is a trademark of many of his stories.

The stories are different because the characters are different. Soapy is older and lacks ambition. Johnsy is young and still desires to paint the Bay of Naples. Soapy is alone without friends to assist him. Johnsy lives in a community of artists and has her dear friend to watch over her. The island represents peace and comfort as a goal for Soapy, but for Mr. Behrman, the painting of the leaf on the wall becomes his goal to paint a masterpiece.